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"When Moe breaks himself romancing a new love, he enlists the aid of Homer in an illegal scheme to collect $5,000 dollars from his automobile's insurance policy. But after Homer botches the scam, Moe must find a way to bust his best customer out of the pen. Guest starring Helen Hunt as Renee."

While at Moe's Tavern, Homer notices Moe's depressed state. After learning Moe has not had a date in some time, he decides to take him out to a night club to meet women. However, the trip proves to be unsuccessful for Moe. When leaving, a woman named Renee (Helen Hunt) who runs a flower stand starts to talk to Moe. Complementing Moe, and making him feel better, it encourages Moe to ask her out.

Moe and Renee fall in love, though Moe feels forced to spend an excessive amount of money, thus trying to avoid dissatisfying her. The card's credit is soon maxed out, leaving Moe to brainstorm for an idea to make more money. He decides to commit insurance fraud by having Homer steal his car and abandon it on rail tracks leaving a train to destroy it. The night of the event, Moe and Renee go out on the "Police Department's Moonlight Charity Cruise", which assures Homer that he will be safe from any police. However, deciding at the last minute to watch a movie at a drive-in theater instead, he fails to leave the car at the tracks on time. Bent on still trying to destroy the car somehow, Homer gets the idea of driving it off a cliff into a body of water. Unable to get out of the car in time, both Homer and the car plummet down, sinking directly in front of the yacht both the entire Police department and Moe are on.

Sent to jail, Homer is then assured that Moe will bail him out. Moe meets Homer outside the jail, talking to him through his jail window. Promising to bail Homer out at first, Moe instead changes his mind while talking to Renee, ultimately deciding upon buying Renee a trip to Hawaii. While packing, Moe is confronted by his own conscious form of Homer, who makes him feel bad for betraying him. Confessing everything to Renee, she reveals that, even though she is glad for Moe telling the truth, she is also disgusted by his actions when learning Moe's plan to save Homer involves even more criminal activities. Still constructing a plan as Renee leaves, Moe figures out a part of his plan involves covering his bar in alcohol to light on fire. Still preparing, Moe drops a match by accident, soon engulfing the bar in flames. Meanwhile, Homer has escaped jail on his own, planning his revenge on Moe. As he arrives at the bar, the two start to fight, but soon lose consciousness due to the excessive smoke. Fortunately, Barney passes by, saving both of them. The bar however, is left completely destroyed, having Homer promise Moe he can use his house as a bar until he is able to have his old bar rebuilt.